History Main / WholesomeCrossdresser

* ''Webcomic/EightBitTheater'': Red Mage, the delusional {{Munchkin}}, has a tendency to cross dress and pretend to be a woman named Deborah. He [[FreudianExcuse blames his father]] for this, but Thief states that he himself managed to put those memories into Red Mage's mind somehow.
** Obviously, he [[{{Pun}} stole them into it]].

* ''Webcomic/JetDream'':Dana and other Elle-Boys in the RemixComic always dress as females but are fairly chaste and strictly heterosexual, apparently due to the (fictional) publisher's misguided attempt to pass UsefulNotes/TheComicsCode and/or [[AuthorAppeal Publisher Appeal]].

* Creator/NnediOkorafor:
** Jacob from novel ''Lagoon'' is simply fascinated by women's fashions, the cuts, the colors, the fabrics - he thinks men's clothes are simply boring. In Nigerian society, it is enough to make him suspect but he is shown as a decent guy.

* ''VisualNovel/{{Utawarerumono}}'': Dori and Gura, though this is only revealed in the game. Even then it is still confusing, as they are the ONLY males shown in the whole series to have tails. At the very least they seem to like men...

* ''Website/{{Literotica}}'': Par for the course in any story on the website that's in the Transsexuals/Crossdressers section and doesn't contain either [[GenderBender magic]] or {{bondage|IsBad}}.

* Roger from ''WesternAnimation/AmericanDad''. He himself is ''anything'' but [[JerkAss wholesome]], but his frequent cross-dressing is never portrayed negatively.

* Stewie in ''WesternAnimation/FamilyGuy'' has taken to this lately. While the most prominent example is Season 5's "Boys Do Cry", in which he dresses as a girl to escape a witch-hunting mob and ends up entering a beauty pageant during the Griffins' stay in Texas, he also dressed up in another episode and pretended to be Brian's girlfriend to spark jealousy on another girl. Men at the restaurant recognized his female persona, so he's obviously used it at least once before.

* ''WesternAnimation/SpongeBobSquarePants'' crossdresses surprisingly often, and seems to enjoy it quite a bit. Whenever [=SpongeBob=] and Patrick need to pretend to be a male and female couple, [=SpongeBob=] will almost always be the female (although it's partly because Patrick [[HalfDressedCartoonAnimal doesn't wear a shirt]]).
* Marco Diaz from ''WesternAnimation/StarVsTheForcesOfEvil'' crossdressed to infiltrate St. Olga's Reform School For Wayward Princesses. He not only leads a rebellion but his Princess Turdina persona becomes an IconOfRebellion and he receives monthly royalty checks for merchandise. When Miss Heinous exposed him to the other princesses (right when he was about to confess the truth himself, ironically enough), the princesses are accepting of the revelation, saying he can be a princess if he wants to. Even Marco's own parents don't bat an eye when he puts on his Turdina facade in front of them. It's gotten to the point that one of the show's most common fan theories is that Marco is actually a [[TransAudienceInterpretation closeted]] UsefulNotes/{{Transgender}} woman.

** In "Sadie's Song", Steven happily dresses up in a crop top, skirt, and makeup when serving as a last-minute substitute for Sadie Miller's musical performance. He's completely comfortable with this, and it's portrayed as the correct thing to do. Nobody judges him for it or even reacts to his attire, and it's not played for laughs or creep factor at all - the only comical part of this situation is that the audience had already guessed the "mystery act" would be Steven ''before'' the substitution was actually made.
** In "Diamond Days", Steven [[spoiler:has the Pebbles make a version of Pink Diamond's outfit in his size for him to wear at the ball]] because he feels he should "dress for the occasion". He doesn't seem to mind wearing it. The only factor that ever makes this uncomfortable for anybody is [[spoiler:the fact that he's [[IAmNotMyFather being shoehorned into his mother's old role on Homeworld]] during this arc.]]

* ''Film/{{Tootsie}}''. While Dustin Hoffman starts out playing a woman simply in order to get work, he ends up playing the part in real-life as well.

** Bridget's arcade mode story ''-STRIVE-'' sheds this trope entirely. Having succeeded in proving her masculinity, she had tried living as a man, only for it to [[TransTribulations trigger her gender dysphoria]], which causes her to leave home once again to figure herself out. After much introspection and confidence building, she [[ComingOutStory comes out]] as a UsefulNotes/{{transgender}} woman.

* The heroine of the bodice-ripper ''Whisper To Me Of Love'' is revealed to be this when her disguise comes off while she's grappling with a would-be victim (she's a pickpocket). She admits to disguising herself as a boy to escape the advances of degenerates (but given the CrapsackWorld that the slums of London area depicted as, this probably wouldn't keep her much safer).

* ''WebVideo/EmpiresSMP'': {{Exaggerated|Trope}} in Seaosn 2. At Gem and Katherine's Princess Tea Party, every attendee is [[DressCode required to show up in a dress]], or be kicked out and shamed across the server, [[DraggedIntoDrag regardless of their gender]]. Not only does every male server-member show up (which would be 8/13 of the season's main cast), but all of them are neutral, if not outright enthusiastic about showing up in a pretty dress, and a couple of them have canonically worn dresses of their own volition prior to the event.

* ''StoryOfSeasonsAWonderfulLife'' allows the player to pick either Shion or Maya's outfit from the start and purchase the other later, gender choice notwithstanding. Other outfits can be purchased from Van, again regardless of gender.

* Out of all the characters in ''Literature/{{Anpanman}}'', tough guy Kamameshidon is the character on the heroes side that is the most likely to crossdress. When he gets a starring episode with a female character, it's very likely that he'll end up crossdressing as her. Thanks to his rice bowl head and deep voice...he is not that good at pulling it off. His friends, Tendonman and Katsudonman, have also crossdressed, just not as often as Kamameshidon does. This possibly could all be based on a single IncrediblyLamePun, as "o'''kama'''" is Japanese for a male crossdresser.

* The ChristmasEpisode of ''WesternAnimation/CodenameKidsNextDoor'' opens with the [[HiveMind Delightful Children]] impersonating the Kids Next Door. The Delightful Children include one brown-skinned boy and a chubby girl, they are presumably the ones that dressed as Numbuh 5 and Numbuh 2, respectively.
** Numbuh 5 wore a tuxedo in an early episode.

* [[WordOfGod Oda]] seems to believe this trope is in effect for all the Okama (crossdressers) in ''Manga/OnePiece'' but while his intentions might be good, the depictions can be quite offensive.

** Mr. 2 Bon Clay. His fighting style is even called "Okama Kenpo" (Transvetite Fist Way), and he has no female partner in Baroque Works because "he counts as a man and a woman".

* ''VideoGame/ToukenRanbu'', a game which features {{Anthropomorphic Personification}}s of Japanese swords as young men, has Midare Toushirou, who fights while wearing a dress. It's this way because the weapon he's based on has a wavy line pattern and not a straight one. His powered-up Kiwame form ratchets up the girliness even further, with more frills and ribbons, giving the appearance of a MagicalGirl.